Unit 11 - Organic chemistry Flashcards
Homologous series
A family of compounds that will have the same general formula and similar chemical properties
4 Homologous series
- Alkanes
- Alkenes
- Alcohols
- Carboxylic acids
Functional group
An atom or group of atoms that determines the chemical properties of the compound
General formula for alkanes
C(n)H(2n+2)
General formula for alkenes
C(n)H(2n)
General formula for alcohols
C(n)H(2n+1)OH
General formula for carboxylic acids
C(n)H(2n+1)COOH
Saturated compounds
All single bonds for carbon = C-C
Unsaturated compound
One or more are not single bonds for carbon
Trend with longer CH chains in structural formulas
Stronger intermolecular forces
Structural isomers
Compounds with the same molecular formula but different structural formulae
Suffix for alkanes
- ane
Suffix for alkenes
- ene
Suffix for alcohols
- ol
Suffix for carboxylic acids
- oic acid
Molecular formula for methane
- CH4
Molecular formula for ethane
- C2H6
Ethene formula
C2H4
Ethanol formula
C2H5OH
Ethanoic acid formula
CH3COOH
Product of alkanes reacting with chlorine
Chloroalkanes
Chloromethane composition
CH3Cl
Product of alkenes reacting with bromine
Dibromoalkanes
Product of alcohols reacting with carboxylic acids
Esters and water
4 common prefixes & number of carbon atoms
- Meth - 1
- Eth - 2
- Prop - 3
- But - 4
Fuel
A chemical substance that when reacted releases energy
3 main fuels
- Coal
- Natural gas
- Petroleum - crude oil & hydrocarbon products
Equation for natural gas reaction
Methane + Oxygen –> Carbon dioxide + water
Petroleum composition
- Mixture of Hydrocarbons
- 30% alkanes
Different impurities in petroleum & their boiling points & uses
- Refinery gas - <40˚C - Bottled gas
- Petrol - 40-205˚C - Petrol/gas
- Naphtha - 60-100˚C - Chemical feedstock
- Kerosene - 175-325˚C - jet fuel, paraffin for lighting & heating
- Diesel - 250-350˚C - Diesel fuels
- Lubricating oil - 300-370˚C - Lubricating oils, waxes & polishes
- Fuel oil - 370-600˚C - Fuel for ships. factories and central heating
- Bitumen - >600˚C - Bitumen for roads and roofing
Viscosity
The property of a material describing its resistance to flow as a liquid
Correlation with carbon atoms and boiling point
- More carbon atoms leads to having a higher boiling point
Method of separation for petroleum
Fractional distillation
Correlation with height of fractional tower and boiling point
- Liquids with lower boiling points are at the top
Correlation with viscosity and number of carbon atoms
- More carbon atoms leads to higher viscosity
Correlation with volatility and number of carbon atoms
- More carbon atoms leads to less volatility
Number of carbon atoms per fraction of petroleum
- Gasoline - 5-6
- Kerosene - 10-15
- Lubricating oil - 25-40
- Bitumen - 40+
Bonds in alkanes
- Single covalent bonds
- Saturated
- Strong covalent bonds
Physical properties of first six alkanes (#Carbon atoms, boiling point, state at room temp.)
- Methane - 1 - -161˚C - gas
- Ethane - 2 - -89˚C - gas
- Propane - 3 - -42˚C - gas
- Butane - 4 - -1˚C - gas
- Pentane - 5 - 36˚C - liquid
- Hexane - 6 - 69˚C - liquid
Reaction that needs to happen for alkanes to be used as a fuel
- Combustion - exothermic reaction
- Incomplete combustion - leads to carbon monoxide gas
Substitution reactions with alkanes
When alkanes react with chlorine, a hydrogen atom is replaced with a chlorine atom to make chloroalkanes - UV is needed for activation energy
Substitution reaction
An atom or group of atoms in a molecule is replaced by a different atom or group of atoms
Photochemical reactions
Reactions that need light energy
Cracking
Chemical process that breaks down larger alkane molecules to produce smaller alkane molecules and alkene molecules and hydrogen
Reason for cracking
- Get fuels from large alkane molecules
- Produce alkenes which are used to make polymers/plastics
Conditions needed for cracking
- Heating (500˚C)
- Catalyst
Bonding in alkenes
- Double C=C bond and absence of two hydrogens
- Double bonds can be broken to form single bonds and allow other atoms to be added
- Unsaturated compounds
Correlation with bonding and distance of nuclei
-More bonds/sharing more electrons drawn nuclei closer
Chemical test for unsaturated double bonds in alkenes
- Test with Bromine water
- If water changes from brown to colorless, a double bond has reacted with the bromine
Addition reactions
A chemical reaction when a double bond is broken in an alkene resulting in the addition of atoms to the molecule - one product forms
Hydrogenation
An addition reaction with an unsaturated compound and hydrogen to make a saturated compound - happens at 200˚C with a nickel catalyst
Ethanol addition reaction
Ethene reacted with steam at 300˚C with phosphoric acid as a catalyst - H bonds with a carbon and -OH with another carbon
Product of ethene reacting with bromine
Dibromoethane
Two processes used to make ethanol
- Fermentation - Glucose –> ethanol + carbon dioxide - enzymes in yeast break the glucose down in absence of air at 25-35˚C
- Catalytic addition of steam to ethene - Ethene + Water –> Ethanol at 300˚C and 6000 kPa = 60 atmospheres & phosphoric acid as a catalyst
Properties of ethanol
- Liquid at room temp
- Volatile
- Boiling point of 78˚C
- Highly flammable - blue flame with oxygen
- Releases a lot of heat energy
- Ethanol + Oxygen –> Carbon dioxide + Water
- Substances can dissolve in ethanol - can be used as a solvent
- Contains alkyl part
Uses of ethanol
- Cosmetics & perfumes - can dissolve substances water can’t
- Perfume - High volatility leads to easy evaporation and diffusion
- Fuel - combustion is highly exothermic & can be used as biofuel from crops
- Hand sanitizers - microorganisms can’t survive in ethanol
Pros and cons of fermentation’s sustainability
- Pro - Fermentation uses crops and waste plant material which is sustainable
- Con - Use of crops for fermentation can impact food supply
Pros and cons of hydration’s sustainability
- Con - Hydration uses petroleum from fossil fuels, which will eventually run out
Pros and cons of fermentation’s process
- Con - Fermentation requires ethanol to be produced in batches so it is a stop-start process
Pros and cons of hydration’s process
- Pro - Hydration can produce ethanol continuously to meet market demands
Pros and cons of fermentation’s cost
- Pro - Fermentation can be conducted at low temperatures so it is relatively inexpensive
Pros and cons of hydration’s cost
- Pro - Hydration can produce ethanol in a fully automated factory requiring little human input
- Con - Hydration requires high temperatures and pressure, which is expensive
Pros and cons of fermentation’s product
- Con - Fermentation requires the impure product to be refined by fractional distillation
Pros and cons of hydration’s product
Hydration can yield pure ethanol that does not need further refinement
Most common carboxylic acid
Ethanoic acid - CH3COOH - dissolves in water to make a solution of pH 2.5
Equation for an acid and metal reacting
Acid + Metal –> Salt + Hydrogen
e.g. Ethanoic acid + magnesium –> magnesium ethanoate + hydrogen
Product of ethnic acids forming salts
- Ethanoate ion - CH3COO^-
Equation for an acid and base reacting
Acid + Base –> Salt + water
e.g. Ethanoic acid + Sodium hydroxide –> Sodium ethanoate + water
Equation for an acid and carbonate reacting
Acid + Carbonate –> Salt + Water + Carbon dioxide
e.g. Ethanoic acid + Sodium carbonate –> Sodium ethanoate + water + carbon dioxide
Two methods of oxidizing ethanol to get ethanoic acid
- Acid fermentation - Using bacteria such as acetobacter with enzymes that catalyze the oxidation of ethanol to ethanoic acid and water
- Using acidified potassium manganate(VII) - KMnO4 is a used as a strong oxidizing agent in the presence of sulfuric acid and heat to make ethanoic acid
Properties and uses of esters
- Homologous series
- Used in modern consumer products
- Fragrant - used in flavoring in food and cosmetic products
Esterification
The process of producing and ester by reacting a carboxylic acid and an alcohol in the presence of an acid catalyst
e.g. Ethanol + Ethanoic acid –> Ethyl ethanoate + Water
Describing how ethanol & ethanoic acid make an ester
- C-O bond of the OH hydroxyl group in ethanoic acid breaks
- The O-H bond in ethanol breaks
- the two remaining parts from each molecule join together forming a C-O bond for the ester
- OH and H combine to form water (condensation reaction)
Naming an ester
- First names comes from the alcohol
- Second name comes from the carboxylic acid
Polymerization reactions
When smaller molecules known as monomers build up to form a polymer molecule
Common plastic
Polythene / poly (ethene)
Making polythene
- Addition polymerization
- Very many ethene molecules react together joining end to end to make polytene molecules
Repeat units
- Used to draw the displayed formula of a whole molecule
- Drawn inside brackets with a n to show a very large number of molecules to form the polymer
- Change C=C bond to C-C and draw a line between then and draw brackets around the repeat unit & add n in writing a chemical equation
Condensation reaction
When two smaller molecules join to produce a larger molecule - large and smaller molecule are produced (usually water is the smaller)
Poor methods of plastic disposal
- Land fills - Leachate can contaminate the surrounding area and nearby bodies of water
- Burning - Incineration leads to toxic gases forming e.g. PVC releases acidic hydrogen chloride
Polyamides
- Condensation polymers
- Made from a dicarboxylic acid containing two COOH groups & a diamine that contains two NH2 groups
- Shown as block diagrams
- O-H and H break of to make H2O
Polyesters
- Condensation polymers
- Made of a dicarboxylic acid & a diol containing two OH groups
- O-H and H break off to make H2O
- Shown as block diagrams
Amide link
A chemical bond in a polyamide with a C=O bond and an N-H bond
Ester link
A chemical bond in polyester comprising of a C=O bond and a C-O bond
Common polyester
PET
Functional groups of amino acids
- NH2 group
- COOH group
Meaning of R in an amino acid structure
Represents a side group that is specific to the amino acid e.g. hydrogen for glycine
Occurrences in making an amino acid
- COOH & NH2 group make an amide link
- Molecule of water is eliminated